Chapter 21 - Wade(1)

Chapter 21 - Wade(1) - Introduction to General and Organic...

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Chapter 21 Carboxylic Acid Derivatives Dr. David P. Brown St. John’s University Introduction to General and Organic Chemistry III ______________________________
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Chapter 21 2 Acid Derivatives All can be converted to the carboxylic acid by  acidic or basic hydrolysis. Esters and amides common in nature. => R C O X R C O O C O R' R C O O R R C O NH 2 R C N RCOX (RCO) 2 O RCOOR RCONH 2 RCN
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Chapter 21 3 Naming Esters Esters are named as  alkyl carboxylates . Alkyl  from the alcohol,  carboxylate  from the  carboxylic acid precursor.  isobutyl acetate 2-methylpropyl ethanoate CH 3 CHCH 2 OCCH 3 CH 3 O HCOCH 2 O benzyl formate benzyl methanoate =>
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Chapter 21 4 Cyclic Esters - Lactones Reaction of -OH and -COOH on same molecule  produces a cyclic ester, lactone. To name, add word  lactone  to the IUPAC acid  name or replace the - ic acid  of common name  with - olactone . O O H 3 C CH 3 4-hydroxy-2-methylpentanoic acid lactone α -methyl- γ -valerolactone =>
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Chapter 21 5 Amides Product of the reaction of a carboxylic acid  and ammonia or an amine. Not basic because the lone pair on nitrogen is  delocalized by resonance. H C O N H H H C O N H H _ + Bond angles around N are close to 120 ° . =>
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Chapter 21 6 Classes of Amides 1 °  amide has one C-N bond (two N-H). 2 °  amide or  N -substituted amide has two C-N  bonds (one N-H). 3 °  amide or  N,N -disubstituted amide has  three C-N bonds (no N-H).                                                            =>
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Chapter 21 7 Naming Amides For 1 °  amide, drop  - ic   or  - oic  acid  from the  carboxylic acid name, add  - amide . For 2 °  and 3 °  amides, the alkyl groups bonded to  nitrogen are named with  N - to indicate their  position.  CH 3 CHC N O CH 2 CH 3 CH 3 CH 3 N -ethyl- N ,2-dimethylpropanamide N -ethyl- N -methylisobutyramide =>
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Chapter 21 8 Cyclic Amides - Lactams Reaction of -NH 2  and -COOH on same molecule  produces a cyclic amide, lactam. To name, add word  lactam  to the IUPAC acid  name or replace the - ic acid  of common name  with - olactam . N O CH 3 H 4-aminopentanoic acid lactam γ -valerolactam =>
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Chapter 21 9 Nitriles - C N  can be hydrolyzed to carboxylic acid, so  nitriles are acid derivatives. Nitrogen is  sp  hybridized, lone pair tightly held,  so not very basic. ( p K  about 24 ). =>
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Chapter 21 10 Naming Nitriles For IUPAC  names, add  - nitrile  to the alkane  name. Common
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Chapter 21 - Wade(1) - Introduction to General and Organic...

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